An aerial view of a town with a river, buildings, and surrounding greenery.

Apartments in Chestertown for Rent

Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chestertown apartments

Free daily full breakfast

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (944 reviews)
"Clean and affordable amenities and a decent breakfast!"
United States
Deanna
$107 nightly
The price is $119
Aug 31 - Sep 1
Total with taxes and fees
Comfort Inn & Suites Chestertown
Lobby lounge

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (475 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
$63 nightly
The price is $70
Aug 16 - Aug 17
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very Good, (94 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
$111 nightly
The price is $123
Aug 19 - Aug 20
Total with taxes and fees
The Lodge at Great Oak Landing
Front of property - evening/night

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (180 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
$64 nightly
The price is $70
Aug 9 - Aug 10
Total with taxes and fees
Driftwood Inn
Exterior

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (10 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
$147 nightly
The price is $163
Aug 17 - Aug 18
Total with taxes and fees
Haven Point Inn and Gallery
Lake

6. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (71 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
$200 nightly
The price is $223
Aug 17 - Aug 18
Total with taxes and fees
Inn at Huntingfield Creek
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), bed sheets

7. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (947 reviews)
"Great staff and breakfast crew. Extremely reasonable price, for convenient location."
United States
Jonathan
$100 nightly
The price is $111
Sep 7 - Sep 8
Total with taxes and fees
Quality Inn Grasonville near Kent Island
Exterior

8. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,006 reviews)
"Very clean hotel,beautiful view and great staff."
United States
Jackie
$119 nightly
The price is $132
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio

9. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (400 reviews)
"Complimentary breakfast was a good option"
United States
Mark
$98 nightly
The price is $109
Aug 16 - Aug 17
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior

10. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (631 reviews)
"The room was very clean and the bed was very comfortable. I enjoyed being able to have breakfast without leaving the facility and driving around to find a local restaurant."
United States
April
$83 nightly
The price is $93
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Indoor pool

11. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,005 reviews)
"good for a short stay"
United States
chanel
$115 nightly
The price is $128
Sep 7 - Sep 8
Total with taxes and fees
Best Western Kent Narrows Inn
Reception

12. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,009 reviews)
"We have stayed here several times and this hotel has consistently been a wonderful stay for us!"
United States
walter
$84 nightly
The price is $95
Sep 1 - Sep 2
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Terrace/patio

13. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,004 reviews)
"Me and my husband went for a one year anniversary. Staying at the hilton was wonderful relaxing, everyone was so pleasant and helpful.The restaurants nearby were great. I love the view we'll be coming back again."
United States
Tammy
$147 nightly
The price is $163
Aug 16 - Aug 17
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
Basic Double or Twin Room | Desk, WiFi (free), bed sheets

14. Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.2 out of 10, Good, (17 reviews)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
$54 nightly
The price is $60
Aug 20 - Aug 21
Total with taxes and fees
Motel Edgewood
Lobby

15. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,001 reviews)
"It was very clean and the staff was friendly as well as professional."
United States
LAURENCE
$89 nightly
The price is $100
Sep 6 - Sep 7
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Studio Suite, 1 King Bed with Sofa bed, Non Smoking | WiFi (free), bed sheets

16. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very Good, (1,120 reviews)
"Great place to stay"
United States
Fayaz
$75 nightly
The price is $84
Aug 23 - Aug 24
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Desk, blackout drapes, iron/ironing board, cribs (free)

17. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (557 reviews)
"This facility was very clean. The decor was nice. A great place to stay"
United States
Alan
$78 nightly
The price is $87
Aug 9 - Aug 10
Total with taxes and fees
Ramada Hotel & Conference Center by Wyndham Edgewood
Exterior

18. Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (537 reviews)
"Centrally located lots of restaurants lots of shopping easy on easy off highway and 95 Nice Pl. to stay. I’ll stay there again. Great price."
United States
Terry
$81 nightly
The price is $91
Aug 16 - Aug 17
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG
Lobby

19. Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (681 reviews)
"Good hotel, clean rooms and breakfast!"
United States
Anthony
$94 nightly
The price is $106
Aug 16 - Aug 17
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds (surcharge)

20. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.8 out of 10, (1,004 reviews)
"The room was very decent and clean. The staff was very helpful. There was little housekeeper service during my 4 day stay"
United States
Anthony
$57 nightly
The price is $64
Sep 6 - Sep 7
Total with taxes and fees
Super 8 by Wyndham Havre De Grace Aberdeen Area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Hotel staff were great as well as valet! Very convenient to downtown Annapolis!"
Colleen 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
8,052
Accommodation
79 Apartments
Lowest Price
$60
Highest Price
$223

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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